Entain general counsel Simon Zinger sent letters dated May 15 to six Premier League clubs, asking them to commit to UK-licensed gambling shirt sponsors for the 2026/27 season. The letters raised concerns about Stake's "heavy reliance on cryptocurrency" and alleged BJ88 uses "unregulated payment methods like cryptocurrency" to avoid oversight, while noting several clubs' current sponsors lack UK Gambling Commission licensing.

On April 30, 2026, Treasury Cabinet Secretary John Mbadi submitted Kenya's Finance Bill 2026 to Parliament, proposing annual information returns for virtual asset service providers and reinstating a 20% withholding tax on gambling winnings. The National Assembly opened public participation on May 11, while the bill also outlines wider tax changes including new data-sharing powers for virtual-asset tax information and adjustments to excise measures.

NPR reported May 7, 2026 that an anonymous campaign staffer said they and coworkers regularly bet on Polymarket using internal polling data before it became public, with winnings described as thousands of dollars per cycle. The report is NPR's third Polymarket-focused insider-trading pattern in three months, as lawmakers and regulators debate responses that largely target government offices rather than campaign staff.

On May 11, 2026, U.S. District Judge William M. Conley in Wisconsin found the Ho-Chunk Nation is likely to succeed under IGRA in stopping Kalshi sports event contracts from being offered on the tribe's Indian lands. The Ho-Chunk Nation sued Kalshi and Robinhood entities last August and later sought a preliminary injunction in December 2025; the case also includes a RICO claim and is set for trial on May 24, 2027.

DraftKings and Flutter Entertainment are moving from consumer prediction-market products into market-making, with Q1 2026 earnings updates outlining the shift. DraftKings reported $1.6 billion in Q1 2026 revenue on May 7 and said its Railbird exchange is central to an effort to be a leading market maker before year-end. Flutter posted $4.304 billion in Q1 2026 revenue on May 6 and said it started providing market-making services on a major third-party platform in April while building its own offering.

The NFL began April without an official sportsbook partner after its deals with Fanduel, Draftkings, and Caesars expired at midnight on March 31 without renewals. Talks reportedly stalled over higher pricing for official live data distributed via Genius Sports, as the league also faces a March 24 lawsuit alleging addictive microbetting products.

The Premier League's 2025/26 campaign is set to be the last season featuring gambling brands on the front of matchday shirts, with deals collectively valued at more than £140 million per year. A voluntary agreement reached in 2023 means the ban begins from the 2026/27 season, affecting 11 of the league's 20 clubs as they seek replacement sponsors.